Acetobromo-α-D-glucuronic acid methyl ester CAS 21085-72-3
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- Appearance: White powder
- Assay: 99. 0%min
- Stock: In stock
- Sample: Available
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Acetobromo-α-D-glucuronic acid methyl ester: The Complete Guide
Acetobromo-α-D-glucuronic acid methyl ester for Sale
Basic Info of Acetobromo-α-D-glucuronic acid methyl ester
Acetobromo-α-D-glucuronic acid methyl ester
ACETOBROMO-ALPHA-D-GLUCURONIC ACID METHYL ESTER; 1-Bromo-2,3,4-tri-O-acetyl-α-D-glucuronic Acid Methyl Ester; 1-Bromo-1-deoxy-2,3,4-tri-O-acetyl-α-D-glucuronic acid methyl ester; Acetyl bromide- α- Methyl D-glucuronate
What is Acetobromo-α-D-glucuronic acid methyl ester?
Alpha-D-glucuronic acid methyl ester, also known as acetyl bromide-α-D-glucuronic acid methyl ester, can be prepared from D-glucuronic acid methyl ester by using D-glucuronide as raw material, and then acetylated. Obtain 1,2,3,4-tetra-O-acetyl-D-glucuronic acid methyl ester, and finally brominate to obtain A-D-glucuronic acid methyl ester.
Acetobromo-α-D-glucuronic acid methyl ester Uses
- Acetobromo-α-D-glucuronic acid methyl ester was used to synthesize hmr1098-s-methyl glucuronate, which is a new K-ATP blocker and can be used as a drug to prevent sudden cardiac death.
- Acetobromo-α-D-glucuronic acid methyl ester (cas 21085-72-3) is a useful compound, which can be used to prepare fluorescent probes for human heparanase.
- Acetobromo-α-D-glucuronic acid methyl ester is used to synthesize camptothecin water-soluble glucosidic acid derivatives for cancer prodrug monotherapy and antibody directed enzyme prodrug therapy (ADEPT).
- Acetyl bromide- α- Methyl D-glucuronate is used to synthesize the glucuronic acid prodrug compound of tofatinib, a Janus kinase (JAK) inhibitor, which can be β- The cleavage of glucuronidases, such as those produced by the gastrointestinal microbiome, increases the level of tofatinib at the site of gastrointestinal inflammation and limits the systemic exposure of tofatinib in the treatment of local inflammatory diseases.
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Preparation of Acetobromo-α-D-glucuronic acid methyl ester
- Synthesis of D-glucuronic acid methyl ester. It can be represented by the following reaction formula:
The specific preparation steps are as follows: D-glucurolactone (1) (17.6 g, 0.1 mol) was dissolved in 200 ml of methanol, and cooled to 0 °C. NaOH (100 mg) was added and stirred for 2 hours. The reaction was concentrated to dryness to give methyl D-glucuronate (2) as a white solid (yield 20.8 g, 100% yield).
- Synthesis of methyl 1,2,3,4-tetra-O-acetyl-D-glucuronic acid. It can be represented by the following reaction formula:
The specific preparation steps are as follows: D-glucuronic acid methyl ester (2) (20.8g, 0.1mol) was dissolved in pyridine (45ml) and cooled to below 5°C, then acetic anhydride (54mL, 0.6mol) was added dropwise to maintain stability Not exceeding 10°C, then stirring at room temperature for 3 hours. The reaction was concentrated to dryness and dissolved in 300 mL of dichloromethane, then the organic phase was washed three times with water, dried over anhydrous sodium sulfate and filtered, the filtrate was concentrated to dryness, and 100 mL of methanol was added to precipitate a solid. The solid was filtered to give methyl 1,2,3,4-tetra-O-acetyl-D-glucuronic acid (3) (yield 24.4 g, 65% yield).
- Synthesis of acetyl bromide-α-D-glucurone acid methyl ester. It can be represented by the following reaction formula:The specific preparation steps are as follows: 1,2,3,4-tetra-O-acetyl-D-glucuronic acid methyl ester (3) (15.0 g, 4 mmol) was added to an acetic acid solution of hydrogen bromide (hydrogen bromide The mass percentage of 33%) (60 mL) was kept stable at no more than 10 °C, and then the temperature was naturally raised to room temperature and stirred for 2 hours. The reaction was concentrated to dryness and dissolved with 100 mL of ethyl acetate, then the organic phase was washed three times with aqueous sodium bicarbonate solution, dried over anhydrous sodium sulfate and filtered, the filtrate was concentrated to dryness, and 50 mL of petroleum ether was added to precipitate a solid. The solid was filtered to obtain A-D-glucuronic acid methyl ester (4) (yield 14.3 g, yield 90%).